Sodium Hydroxide → HCID 131717579, compound

Participants

Reaction Steps

To a solution of 7.00 g (22.7 mmol) 5-(cyanomethyl)-2-(difluoromethyl)-4-methyl-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester, prepared as in Example E, in 450 mL dichloromethane was added 6.41 g (45.4 mmol) 4-chlorobutyryl chloride, 0.30 g benzyltriethylammonium chloride, and 135 mL 50% sodium hydroxide. The mixture was stirred for 30 minutes, poured over ice, and extracted with diethyl ether. The organic layer was dried with magnesium sulfate, treated wit decolorizing carbon, filtered through silica gel, and evaporated in vacuo. The residue was recrystallized in ethyl acetate and hexane, yielding 4.59 g of the desired product as a white crystalline solid, a 54% yield. m.p. 160°-161° C.

Provenance & Evidence